WO2019067757A1 - Formulations d'encre et instruments d'écriture associés - Google Patents

Formulations d'encre et instruments d'écriture associés Download PDF

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Publication number
WO2019067757A1
WO2019067757A1 PCT/US2018/053179 US2018053179W WO2019067757A1 WO 2019067757 A1 WO2019067757 A1 WO 2019067757A1 US 2018053179 W US2018053179 W US 2018053179W WO 2019067757 A1 WO2019067757 A1 WO 2019067757A1
Authority
WO
WIPO (PCT)
Prior art keywords
ink formulation
percent
ink
weight
bio
Prior art date
Application number
PCT/US2018/053179
Other languages
English (en)
Inventor
Jiandong Zhu
Original Assignee
Sanford, L.P.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sanford, L.P. filed Critical Sanford, L.P.
Priority to US16/648,830 priority Critical patent/US20200224046A1/en
Priority to CN201880063632.9A priority patent/CN111148802A/zh
Priority to EP18863260.8A priority patent/EP3676339A4/fr
Publication of WO2019067757A1 publication Critical patent/WO2019067757A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/16—Writing inks
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/16—Writing inks
    • C09D11/18—Writing inks specially adapted for ball-point writing instruments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/16—Writing inks
    • C09D11/20—Writing inks indelible

Definitions

  • This disclosure relates generally to ink formulations and associated writing instruments.
  • Certain ink formulations (e.g., for permanent markers, dry erase markers, pens) contain solvents that are petroleum-based and display various performance issues.
  • known ink formulations may display poor writing performance and having limited adhesion on certain substrates. Additionally, known inks may be prone to drying out when left uncapped in a writing instrument for extended periods.
  • the ink formulations may contain a solvent or blend of solvents that is partially or wholly biobased.
  • biobased refers to a solvent that is non-petroleum based and that is derived from a renewable source (e.g., plant source).
  • an ink formulation contains an ink resin or polymer and a solvent.
  • the solvent contains at least one lactate ester, which may or may not be biobased.
  • the solvent is wholly biobased. That is, in certain embodiments, the ink formulation contains no petroleum based solvents.
  • the at least one lactate ester which may or may not be biobased, may be ethyl lactate, methyl lactate, n- or iso-propyl lactates, n- or iso-butyl lactates, i-amyl lactate, and/or 2-ehtylhexyl lactate.
  • a biobased solvent may contain one or more lactate esters or a blend of one or more lactate esters with one or more other solvents selected from esters, alcohols, glycol ethers, limonene and/or aliphatic hydrocarbon solvents.
  • the biobased solvent may be bio-propanol, bio-butanol, bio- methanol, bio-ethanol, biobased polypropylene glycols, biobased ethylene glycols, bio- glycol ethers, bio-based butanediol, biobased propanediol, bio-lactate esters, bio-acetate esters, D-limonene, methyl soyate, 2-methyltetrahydrofuran, and isohexane.
  • the solvent or blend of solvents is present in an amount of from about 35 percent to about 95 percent, by weight of the ink formulation, for example about 35 percent by weight of the ink formulation, about 40 percent by weight of the ink formulation, about 45 percent by weight of the ink formulation, about 50 percent by weight of the ink formulation, about 55 percent by weight of the ink formulation, about 60 percent by weight of the ink formulation, about 65 percent by weight of the ink formulation, about 70 percent by weight of the ink formulation, about 75 percent by weight of the ink formulation, about 80 percent by weight of the ink formulation, about 85 percent by weight of the ink formulation, about 90 percent by weight of the ink formulation, about 95 percent by weight of the ink formulation, or any ranges
  • the solvent is present in an amount of from about 45 percent to about 95 percent, by weight of the ink formulation.
  • the ink resin or polymer is present in an amount of from about 1 percent to about 40 percent, by weight of the ink formulation, for example about 1 percent by weight of the ink formulation, about 5 percent by weight of the ink formulation, about 10 percent by weight of the ink formulation, about 15 percent by weight of the ink formulation, about 20 percent by weight of the ink formulation, about 25 percent by weight of the ink formulation, about 30 percent by weight of the ink formulation, about 35 percent by weight of the ink formulation, about 40 percent by weight of the ink formulation, or any ranges
  • the ink resin or polymer may be present in an amount of from about 3 percent to about 25 percent, by weight of the ink formulation, for example about 3 percent by weight of the ink formulation, about 5 percent by weight of the ink formulation, about 10 percent by weight of the ink formulation, about 15 percent by weight of the ink formulation, about 20 percent by weight of the ink formulation, about 25 percent by weight of the ink formulation, or any ranges therebetween.
  • the resin or polymer may be any suitable ink resin or polymer material, as are known in the art.
  • the ink formulation also includes a colorant present in an amount of from about 3 percent to about 40 percent, by weight of the ink formulation.
  • the colorant may be present in an amount of from about 3 percent to about 25 percent, by weight of the ink formulation, for example about 3 percent by weight of the ink formulation, about 5 percent by weight of the ink formulation, about 10 percent by weight of the ink formulation, about 15 percent by weight of the ink formulation, about 20 percent by weight of the ink formulation, about 25 percent by weight of the ink formulation, or any ranges therebetween.
  • the colorant may be any suitable dye, pigment, or other coloring agent, or combination thereof, which are known in the art.
  • the ink formulation also includes a cap-off agent present in an amount of from about 0.1 percent to about 5 percent, by weight of the ink formulation, for example about 0.1 percent by weight of the ink formulation, about 0.5 percent by weight of the ink formulation, about 1 percent by weight of the ink formulation, about 2 percent by weight of the ink formulation, about 3 percent by weight of the ink formulation, about 4 percent by weight of the ink formulation, about 5 percent by weight of the ink formulation, or any ranges therebetween.
  • the cap-off agent may be any suitable agent configured to prevent the ink formulation from drying out when left in an uncapped writing instrument (e.g., marker, pen).
  • a suitable cap-off agent may be CA 340.2 and/or CA210.2, manufactured by Multichem (United Kingdom), and/or other suitable additives, specialty waxes and/or surfactants that could also function as cap-off agents.
  • the ink formulation also includes one or more additives.
  • suitable additives may include UV stabilizers, adhesion promoters, and releasing agents, which are known in the art.
  • writing instruments containing the ink formulations described herein are also provided.
  • the writing instrument may be any suitable type of writing instrument design known in the art, such as permanent markers, dry erase markers, and pens, including ballpoint pens.
  • the writing instrument may contain the ink formulation in a suitable reservoir configured to deliver the ink to a nib or instrument tip, for delivery onto a substrate.
  • the writing instrument displays a cap-off time (i.e., time after which a writing instrument containing the ink formulation becomes unusable/dried out when the instrument is left uncapped) of at least 3 hours. In some embodiments, the writing instrument displays a cap-off time (i.e., time after which a writing instrument containing the ink formulation becomes unusable/dried out when the instrument is left uncapped) of at least 3 hours.
  • xylene was used as the solvent.
  • xylene displays good solubility for oil soluble dyes, ink resins and/or ink polymers.
  • Some xylene based permanent ink markers are still used in specialty writing products because the maker inks based on xylene display fast drying and can write through/on watery/wet surfaces, although not well on oily surfaces.
  • xylene displays a toxicity such that it is not desirable for use in a general purpose marker ink formulation.
  • many permanent marker ink formulations now use alcohol-based solvent that display reduced writing performance.
  • such markers typically have less than one hour of cap-off time (i.e., time after which a writing instrument containing the ink formulation becomes unusable/dried out when the instrument is left uncapped).
  • cap-off time i.e., time after which a writing instrument containing the ink formulation becomes unusable/dried out when the instrument is left uncapped.
  • the disclosed ink formulations have been developed to provide improved permanent maker inks with lactate esters, blends of lactate ester with other esters (such as acetate esters and/or propionate esters), alcohols, glycol ethers and/or hydrocarbon solvents.
  • the improved permanent ink with lactate esters and its blend with other solvents were found to write better on both wet and oily surface than xylene based permanent maker inks for industrial uses.
  • some fade resistance dyes and hydrophilic resins, which are normally not soluble in xylene, were discovered to also be usable in the disclosed permanent marker inks to further enhance fade resistance and the ability write on oily surface or ink permanence on oily surface.
  • the weight percent of lactate ester or ester blends and/or blends of lactate esters with other solvents in the ink formulation is from 45% to 95%.
  • These permanent marker ink formulations for industrial usages not only displayed improved ink performance but are also more environmentally friendly and more sustainable when one or more or all the lactate esters and other solvents in the blends (other esters, glycol ethers, alcohols and hydrocarbon solvents), and/or the resin/polymer and additives are bio-based or from renewable resources.
  • cap-off agents such as CA 340.2
  • CA 340.2 may be used to extend ink marker cap-off time up to more than 10 hours, while, in contrast, there is no commercially available cap-off agent for xylene-based marker inks.
  • the disclosed ink formulations use lactate esters and/or blends of lactate esters with d-limonene, and/or alcohols in the improved permanent marker inks for general usages.
  • lactate esters and blends of lactate esters with other solvents broadens the choices of ink resin/polymers and ink dyes, especially some fade resistance dyes which is normally not soluble in lower alcohols, and improves ink performance with better fade resistance and adhesion.
  • Table 2 The Exemplary Permanent Marker Inks for General or Consumer Use
  • the weight percent of lactate ester or esters and/or blends of lactate esters with other solvents in the ink is from 45% to 95%.
  • the disclosed permanent marker inks for general usages were found not only to display improved ink performance but are also more environmentally friendly and more sustainable when one or more or all the lactate esters and other solvents in the blends and/or the resin/polymer and additives are bio-based or from renewable resources.
  • the cap-off agents such as CA 340.2 and/or CA210.2, can be added into these permanent marker inks for general usages to extend ink cap off time to more than 5 days although the cap-off agents are not necessary for the invented marker inks to have sufficient cap-off time (less than 2 hours) for normal general usages.
  • dry erase marker ink formulations were prepared using lactate esters and/or their blends with other esters, alcohols and other solvents. These dry erase inks were found to have similar dry erasability as ketone based dry erase inks without strong ketone odor and toxicity.
  • the weight percent of lactate ester or esters and/or blends of lactate esters with other solvents in the ink is from 45% to 95%.
  • the disclosed dry erase marker inks were found to not only display improved ink performance but are also more environmentally friendly and more sustainable when one or more or all of the lactate esters and other solvents in the blends (other esters, alcohols, glycol ethers), and/or the resin/polymer and additives are bio-based or from renewable resources.
  • cap-off agents such as CA 340.2 and/or CA210.2, including additives, specialty waxes and/or surfactants which could function as cap-off agents, could be added into the invented dry erase marker inks to extend ink cap off time.
  • ethylene or propylene glycol ether solvents such as diethylene glycol monoethyl ether/glycol ether DE or ethylene glycol phenyl ether (EPH)
  • benzyl alcohol are used.
  • These solvents are currently produced from petroleum/fossil sources and may contain toxic residue of ethylene oxide or propylene oxide (for glycol ether based solvents) and toluene (for benzyl alcohol).
  • ball point pen ink formulations were prepared using lactate esters, blend solvents of lactate esters with d-limonene, alcohols and other solvents. These inks were found to provide wider choices of ink dyes and ink resins/polymers. For example, it was discovered that the formulations could include fade resistant dyes and more durable resins/polymers to increase ball point pen ink resistance properties, such as color fading resistance.
  • the weight percent of lactate ester or esters and/or blends of lactate esters with other solvents in the ink formulation is from 35% to 99%.
  • the disclosed ball point pen inks were found not only to display improved ink performance but also are more environmentally friendly and more sustainable when one or more or all of the lactate esters and other solvents in the blends (other esters, alcohols, glycol ether) and/or the resin/polymer and additives are bio-based or from renewable resources.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

L'invention concerne des formulations d'encre et des instruments d'écriture associés. Dans certains modes de réalisation, l'invention concerne une formulation d'encre qui comprend une résine ou un polymère d'encre et un solvant d'origine biologique. Dans certains modes de réalisation, l'invention concerne une formulation d'encre qui comprend une résine ou un polymère d'encre, ainsi qu'un solvant comprenant au moins un ester de lactate.
PCT/US2018/053179 2017-09-29 2018-09-27 Formulations d'encre et instruments d'écriture associés WO2019067757A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US16/648,830 US20200224046A1 (en) 2017-09-29 2018-09-27 Ink Formulations and Associated Writing Instruments
CN201880063632.9A CN111148802A (zh) 2017-09-29 2018-09-27 油墨制剂和相关的书写工具
EP18863260.8A EP3676339A4 (fr) 2017-09-29 2018-09-27 Formulations d'encre et instruments d'écriture associés

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201762565317P 2017-09-29 2017-09-29
US62/565,317 2017-09-29

Publications (1)

Publication Number Publication Date
WO2019067757A1 true WO2019067757A1 (fr) 2019-04-04

Family

ID=65903600

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2018/053179 WO2019067757A1 (fr) 2017-09-29 2018-09-27 Formulations d'encre et instruments d'écriture associés

Country Status (4)

Country Link
US (1) US20200224046A1 (fr)
EP (1) EP3676339A4 (fr)
CN (1) CN111148802A (fr)
WO (1) WO2019067757A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021067267A1 (fr) * 2019-10-01 2021-04-08 Sanford L.P. Encres effaçables à sec et instruments d'écriture associés

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02294372A (ja) 1989-05-08 1990-12-05 Mitsubishi Pencil Co Ltd マーキングペン用インキ
US5961703A (en) * 1997-08-15 1999-10-05 J.S. Staedtler Gmbh & Co. Aqueous ink having an extended cap-off time and process of manufacture thereof
US5981626A (en) 1997-02-14 1999-11-09 Binney & Smith Inc. Washable coloring composition suitable for use in dry erase markers
WO2007021377A2 (fr) 2005-08-16 2007-02-22 Electronics For Imaging, Inc. Encres d'impression par jet d'encre, procedes d'application d'encre d'impression par jet d'encre, et articles imprimes a l'aide d'encres d'impression par jet d'encre
GB2461147A (en) 2008-05-20 2009-12-30 Sericol Ltd Inkjet printing ink composition and method
US20110009518A1 (en) * 2009-07-08 2011-01-13 Nippon Bee Chemical Co., Ltd. Photosetting type bio-based coating composition and its coated article
WO2014042623A1 (fr) 2012-09-12 2014-03-20 John P. Nissen Jr. Company Composition de marquage solide

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2914669B1 (fr) * 2012-11-02 2018-12-05 Domino Printing Sciences PLC Composition d'encre pour impression par jet d'encre
JP6055276B2 (ja) * 2012-11-05 2016-12-27 クラリアント・インターナシヨナル・リミテツド 遮熱塗料用黒色顔料組成物、それを用いた遮熱塗料、並びに調色、塗装のためのそれの使用

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02294372A (ja) 1989-05-08 1990-12-05 Mitsubishi Pencil Co Ltd マーキングペン用インキ
US5981626A (en) 1997-02-14 1999-11-09 Binney & Smith Inc. Washable coloring composition suitable for use in dry erase markers
US5961703A (en) * 1997-08-15 1999-10-05 J.S. Staedtler Gmbh & Co. Aqueous ink having an extended cap-off time and process of manufacture thereof
WO2007021377A2 (fr) 2005-08-16 2007-02-22 Electronics For Imaging, Inc. Encres d'impression par jet d'encre, procedes d'application d'encre d'impression par jet d'encre, et articles imprimes a l'aide d'encres d'impression par jet d'encre
GB2461147A (en) 2008-05-20 2009-12-30 Sericol Ltd Inkjet printing ink composition and method
US20110009518A1 (en) * 2009-07-08 2011-01-13 Nippon Bee Chemical Co., Ltd. Photosetting type bio-based coating composition and its coated article
WO2014042623A1 (fr) 2012-09-12 2014-03-20 John P. Nissen Jr. Company Composition de marquage solide

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021067267A1 (fr) * 2019-10-01 2021-04-08 Sanford L.P. Encres effaçables à sec et instruments d'écriture associés
US11753558B2 (en) 2019-10-01 2023-09-12 Sanford, L.P. Dry erase inks and associated writing instruments

Also Published As

Publication number Publication date
CN111148802A (zh) 2020-05-12
US20200224046A1 (en) 2020-07-16
EP3676339A4 (fr) 2021-07-28
EP3676339A1 (fr) 2020-07-08

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